Looking for the Hamptons? Go the Other Way

At the end of the line, the very last stop on the Long Island Rail Road, there is a huge rusted anchor. Beyond it, there is water and there are boats. The ferry to Shelter Island chugs back and forth, a purposeful ship among the flighty sailboats.

We had arrived in Greenport, N.Y., on a late-summer afternoon not by rail, ferry or yacht, but by tiny hatchback. So when we found ourselves stepping over train tracks near the waterfront later that night, my husband, Tim, did not believe at first that they belonged to the L.I.R.R. Though we had driven only two hours from our apartment in New York City, Greenport, at the far end of the North Fork on the island’s East End, felt as far away as Maine, as distant as the Oregon coast.

Indeed, the North Fork feels more culturally akin to the fishing villages of New England or the Pacific Northwest than to the haughty cosmopolitanism of the Hamptons or the sophisticated art and food scenes of the Hudson Valley. To relatively recent New York transplants like Tim and me, the idea that a $19.75 train ticket and a straight shot from Penn Station could deposit us among fish shacks and farm stands, upstart breweries and biodynamic vineyards, seemed somehow unreal.

With its deepwater bay and sheltered channel, Greenport has been home to one sea-centric industry after another: from whaling to shipbuilding, menhaden fishing to oyster processing. In Greenport’s 175-year existence as an incorporated village, the surrounding area has changed relatively little. The railroad, which was completed in 1844, helped establish the local economy by giving East End farmers access to city markets.

The most notable change over the last several decades is the number of vineyards — ones with ever-growing reputations — that have begun to encroach on Long Island’s established crops. But the fields of potatoes, white corn and berries are still there, being cultivated alongside the North Fork’s 40 or so wineries. Most of the farm stands are open well into fall, when the weather cools, the pumpkin patches open and the wineries celebrate their harvests.

To get to Greenport, we had driven past the suburbs and the pine barrens to where the highway turns from eight lanes to two and the roadsides open into farmland. At the end of driveways, there were hand-scrawled advertisements for fresh eggs and raw milk. One modest stand brought us to an abrupt stop with a sign for Holy Schmitt’s fresh horseradish mustard, a bracing condiment that has become a household favorite.

These brake-screeching moments happened again and again during our three days on the North Fork. It was a pattern of enthusiastic bad behavior that, I can only imagine, contributes to the local perception of people like us — urbanites in town for the weekend or an overnight. We’re referred to as “cidiots,” I was told: city idiots.

It’s a nickname I learned from Peter Pace. Mr. Pace grew up in working-class Hell’s Kitchen, went on to success on Madison Avenue and, two years ago, started one of Greenport’s better restaurants, First and South, with his business partner, Sarah Phillips. A frenetic, comically gregarious 48-year-old with a shaved head and a fondness for sherbet-toned sweaters, he seems to savor his own cidiot status. I met Mr. Pace when, coincidentally, we sat a couple of tables over from him at Love Lane Kitchen in Mattituck, about 20 minutes west of Greenport, the morning after having happy-hour drinks at First and South. Recognizing us from the night before, he struck up a conversation and, before long, insisted on showing us around.

A half-hour later, Mr. Pace was driving us down narrow farm lanes and apologizing again and again for the weather, as if the threatening clouds were a personal failing. He took us past “Private Road” signs and through a dense wall of vine-choked trees until we came upon an elegant home, large yet unobtrusive, with stunning views of the pacific blue of Long Island Sound.

His point: the most sublime places on the North Fork are ones like this — hidden spots, side roads, even graveyards. As we drove on, Mr. Pace practically yelped at the sight of aging potato trucks on Oregon Road, lined up side by side. (“A photographer’s dream come true,” he said.)

But I was more interested in what those tractors helped produce, what the boats pulled in, what the farm stands sold and what the wineries poured. With so much to eat and drink, and only three days to do it, the North Fork had thrown me into a gluttonous frenzy.

On our first night in Greenport, Tim and I had done what city people do in seaside towns in the summertime: we walked the waterfront, inhaling briny air in deep gulps. We passed the ice cream shop, with a line out the door; the famous century-old carousel (now housed in its own pavilion), closed for the night; and the vintage seafood restaurants. Nearby, the town’s former train station, built in 1894, has been converted into a maritime museum, a repository of retired lighthouse lenses and antique sextants. At night, its roof is lighted with blue neon, which cast a nostalgic glow through the fog.

Beyond, aging fireboats and modest pleasure craft rested alongside impossibly opulent megayachts. We gawked at their dimensions, watched tiny fish school at their waterline and laughed at the “Private: Do not board” sign hung above the deck. Having spent a lot of money on a mediocre meal at a new restaurant called Main Restaurant and Oyster Bar, Tim and I felt disenchanted by the lifestyles of the rich and famous, and so focused the remainder of our dining at takeout windows and deli counters.

There was the complex, if untraditional, pozole at the Lunch Truck, an RV parked behind a painted mural of a cartoonish farmscape in the parking lot of the North Fork Table & Inn in nearby Southold, which is said by many to be the area’s best restaurant. At Fork & Anchor, in East Marion, there were uncommonly flavorful deli sandwiches, including one that combined truly crispy chicken with sriracha mayonnaise. At the Winemaker Studio in Peconic, there were simple, satisfying small plates to accompany North Fork wines. The sit-down exception to all these casual meals would be a return visit to First and South. On the front patio, we ate a fried calamari dish, with candied lemons and smoked yogurt, and a generous burger topped with house-made kimchi.

In between, there were reds, whites and rosés, Greenport Harbor Brewing beer and even a vodka tasting at Long Island Spirits, which looks out over potato fields. Our final stop was Shinn Estate Vineyards, one of the first wineries to make a name for itself on the North Fork. David Page, who started the winery with his wife, Barbara Shinn, in 1998, is both furiously passionate about his creations and inclined toward experimentation. An early adopter of sustainable winemaking, Shinn is powered solely by the sun and wind. Though Mr. Page bought a 400-liter copper still from Portugal three years ago and began producing brandy and grappa, he is still very much a winemaker.

In his cellar, which is built of salvaged heartwood pine from a circa 1870 barn, he held his ear to a barrel of his wild fermented merlot, listening to the “healthy, natural populations of yeast.” Tim and I took turns doing the same; it crackled like Pop Rocks. Then Mr. Page poured a small taste into a glass. It’s “honest juice,” he said, proud of the simplicity of his process, the lack of “inputs,” as he calls the additives most wines contain. “All it is is juice in a barrel.”

But Mr. Page also sees wine as the harbinger of a sophisticated local culture.

“If you had gone to the Napa Valley in 1975, there were these guys growing grapes, but you couldn’t go out to a restaurant,” he said. “So it’s the wine of the region, and then the food that gives us cuisine, and from that can grow culture. That’s what’s happening here.”

IF YOU GO

WHERE TO STAY

For the bed-and-breakfast treatment, Fordham House (817 Main Street, Greenport, N.Y.; 631-477-8998; fordhamhouse.com), in a former shipbuilder’s home from 1901, offers three rooms (starting at $275 on weekends), a wraparound porch and lawn croquet out back.

Greenporter Hotel (326 Front Street, Greenport; 631-477-0066; thegreenporter.com) is a former motor lodge that has been renovated and expanded, but remains a relatively affordable option. Rates from $159.